Sodium hydride → 2-Benzoyl-4-oxo-4-pyridin-3-yl-butyronitrile

HRID 2121688Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2121688
[C:1]([CH2:9][C:10]#[N:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br.Br[CH2:16][C:17]([C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)=[O:18]>C1COCC1.[Cl-].[Na+].O>[C:1]([CH:9]([CH2:16][C:17](=[O:18])[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1)[C:10]#[N:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 64799BenzoylacetonitrileHCID 27762343-(2-Bromoacetyl)pyridine hydrobromide

Produkt 1

HCID 112885272-Benzoyl-4-oxo-4-pyridin-3-yl-butyronitrileAusbeute 98,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To 3.0 g (21 mmol) of benzoyl acetonitrile in 50 mL of THF, cooled in a wet ice bath, was added 0.84 g (21 mmol) of sodium hydride (60% oil dispersion). After 1 h, added 2.8 g (10 mmol) of 3-bromoacetylpyridine hydrobromide. After 3 h, poured the reaction mixture into brine, extracted with ethyl acetate, dried over sodium sulfate, concentrated under reduced pressure and purified by flash chromatography (gradient elution: 40-80% ethyl acetate/hexane) to give 2.6 g (93%) of 2-benzoyl-4-oxo-4-pyridin-3-yl-butyronitrile (MH+=265).

Aufarbeitung

  1. waitAfter 3 h
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. custompurified by flash chromatography (gradient elution: 40-80% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-0586360f79824cd29f754130c5eaafff
Quelldatensatz
uspto-grants-2004_02
Patentnummer
US06696471B2

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